


Silks and Lace

by TheatricArcana



Category: Critical Role (Web Series)
Genre: Dom Caleb Widogast, Established Relationship, Guided masturbation kinda, Lingerie, M/M, More trans shadowgast... it's what we deserve, Rough Sex, Strap-Ons, Trans Caleb Widogast, Trans Essek Thelyss, Trans Male Character, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-10-13
Updated: 2020-10-13
Packaged: 2021-03-07 21:00:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,319
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26984041
Author URL: https://archiveofourown.org/users/TheatricArcana/pseuds/TheatricArcana
Summary: Caleb's hands were already twitching at his side as Essek stalked slowly closer, Caleb barely resisting the urge to reach out and touch. He was hardly able to bite back a whimper at the mere sight of Essek."Do you like it?" Essek asked, a coy little grin on his face because he knew Caleb liked it, he just wanted to hear Caleb say it."I…" Caleb could not find the words to describe how Essek looked. There was no word in any language that Caleb knew that could possibly explain how exquisitely divine Essek was in this moment. Caleb was confident he could read every last book from the archives of the cobalt soul and still not find the words or a language suitable to properly tell Essek how gorgeous he was.He had to try, though.(Caleb comes back to Rosohna after being gone for a week, and Essek summons Caleb to his house late at night for a surprise. The "surprise" is that he's wearing lingerie. I'm sure you can guess where it goes from there.)
Relationships: Essek Thelyss/Caleb Widogast
Comments: 2
Kudos: 109





	Silks and Lace

**Author's Note:**

> This was supposed to be a short drabble describing Essek in lingerie and got out of hand, enjoy!! 
> 
> As far as setting uhhhh??? It's based in the future and Caleb (and probably the rest of TM9) stays in Rosohna more frequently, and Caleb is really only away from Essek for extended periods when he's on important missions that use up all his spell slots.
> 
> I use words that are more commonly associated with being feminine to describe Essek (cunt, breasts, yknow), and words that are more commonly associated with being masculine to describe Caleb. They're both trans men, though Essek experiences little to no dysphoria, meaning wearing lingerie doesn't make him uncomfortable.
> 
> As always, gentle constructive criticism and positive feedback is always appreciated <3

Caleb hadn't known exactly what he should have been expecting when he summoned to Essek's residence in the late hours of the evening, but it certainly wasn't this. Caleb had a thousand questions crop up in his mind as he watched Essek gracefully descend the staircase, but he was unable to voice any of them, words entirely failing him at the scene before him. He stared helplessly at Essek, in complete awe, desperately attempting to commit every last detail of the image before him to his memory. It wasn't hard, Caleb was fairly confident he would never forget this.

Caleb's soft gasp upon seeing Essek was audible in Essek's quiet foyer. Caleb could see the subtle upturn of Essek's lips when he heard Caleb's reaction, as Essek knew exactly why Caleb responded the way he did.

Essek looked  _ luxurious _ . The fine silk robe he was wearing was long enough to trail just a couple inches on the floor behind him elegantly, and was parted in the front to reveal the outfit underneath. The robe, beautiful as it was, was surely meant for nothing more than decoration. The sheer fabric looked as if it would do little to protect against a chill despite the long, elegant sleeves that got wider towards the ends. It was the same white color as Essek's hair, and stood out boldly against Essek's dark skin.

The silk garment would have made Essek look nice on its own. Partially because Essek simply looked good in anything, and partially because it didn't take a professional seamstress to tell that the robe was very nice quality, and therefore was made to look nice on anyone. Caleb was sure Essek had it specially tailored for him as well, making sure it showed off all the right areas and draped perfectly over his body. However, despite all that, the silk robe wasn't the thing making Essek look incredible at the moment.

It was what was  _ underneath _ the robe that made Caleb's words fail him.

White lace clung to Essek's skin in the form of a balconette brassiere, showing off the slight curve of Essek's small breasts. Caleb could see fading hickeys from the last time he had visited Essek privately peeking out from under the sheer fabric, which only served to fuel the heat that was slowly growing under Caleb's clothing, the room suddenly feeling uncomfortably warm as he dragged his eyes down Essek's slender form.

Essek was wearing a garter belt made from the same lacey material as the bralette, and it held up the delicate, gossamer material that covered Essek's legs up to his mid-thighs. There were similar lace embellishments at the top of the thigh-highs as well, which matched the expensive looking lace of the underwear that Essek was wearing. The underwear was hardly modest, the fabric barely enough to cover the most important parts, but Caleb knew Essek's goal tonight was anything but  _ modest _ .

Everything was stark white, a stunning contrast against Essek's deep, midnight skin. The entire matching set was probably made with the finest silks and best lace available in Xhorhas, presumably put together by the most skilled and professional hands Essek could find, and Caleb was painfully aware of the fact that Essek's lingerie was  _ definitely  _ worth more than any single item he owned. Especially considering all the jewelry Essek had yet to take off, white jewels and diamonds shining and glittering when they caught the warm, dim light.

Essek looked like a  _ bride _ , Caleb thought. All dressed up in fine whites and beautiful, expensive fabric. He was a delicacy that Caleb felt like he shouldn't be able to afford, an indulgence that was far too nice for anything Caleb deserved, but here Essek was in front of him regardless, even more devastatingly stunning than usual. As it was, Caleb's hands were already twitching at his side as Essek stalked slowly closer, Caleb barely resisting the urge to reach out and touch. He was hardly able to bite back a whimper at the mere sight of Essek.

"Do you like it?" Essek asked, a coy little grin on his face because he  _ knew  _ Caleb liked it, he just wanted to hear Caleb say it.

"I…" Caleb could not find the words to describe how Essek looked. There was no word in any language that Caleb knew that could possibly explain how exquisitely divine Essek was in this moment. Caleb was confident he could read every last book from the archives of the cobalt soul and still not find the words or a language suitable to properly tell Essek how gorgeous he was.

He had to  _ try _ , though.

"I- My love, you are..." Caleb started, locking eyes with Essek before continuing "You are  _ gorgeous,  _ my love. You are divine. There are no words strong enough to appropriately describe how stunning you are."

Essek would never admit it, but Caleb could see the way Essek preened under his flattery, the barest hint of a blush visible on Essek's cheeks now that he was closer to Caleb. Essek only continued to get closer as well, stopping right before Caleb only to stand on his toes and wrap his arms around Caleb's neck. Caleb instinctively slid an arm around Essek's waist to pull him in even closer, until Essek's barely-clothed form was pressed firmly up against his. He made sure to slip his hand underneath Essek's robe just so he could feel Essek's bare skin, caressing his waist with callused fingers, making Essek shiver.

"Then don't use words,  _ show me _ ."

Caleb was slowly starting to get his nerve back now that the initial shock had worn off, and he was getting  _ hungry _ . He was starved for Essek's soft skin- it had been a week since Caleb had last seen him, and Essek had taken the generous liberty of wrapping himself in beautiful lace like a delicate present, and Caleb's hands desperately wanted to  _ unwrap _ that present.

Caleb let his hand rest on the back of Essek's neck, sliding his other up the soft, warm skin of Essek's back. Despite Essek being on his toes, Caleb still had to lean down slightly to fill the last inch or two of space between them.

The light colored fabric Essek wore made him look oddly… innocent, which was not a word that Caleb ever thought he would associate with the shadowhand. It was what came to mind when he saw the white material, though. The outfit, despite its inherent sexual nature, was also somehow a perfect visage of purity and innocence. 

Which only made it that much more arousing when the way Essek kissed him was anything  _ but  _ pure and innocent.

Within seconds they were desperately clinging to each other, hungry for the other and impatient from how long it had been since they had last done this. Essek's teeth caught Caleb's lip, and Caleb groaned softly in response before he was leaning down even further, mouthing down Essek's throat and grabbing the underside of Essek's thighs, lifting Essek with ease despite his lack of muscle. Essek hardly weighed anything. He was slender and barely five feet tall, meaning Caleb was able to lift him without much trouble, and Essek  _ certainly _ didn't air any complaints about being held by Caleb. If anything, it only invigorated Essek, as Essek was now deepening the kiss even more so, wrapping his slim legs around Caleb's waist to keep himself in place. 

Caleb took Essek up the stairs, running on muscle memory as he made his way towards Essek's bedroom. Essek let out a soft noise of surprise when Caleb practically threw him down onto the bed, causing Essek to bounce gently on the mattress a few times before coming to rest. Caleb stood at the edge of the bed, unable to resist drinking in the sight before him, indulging himself in another long look at Essek.

Essek looked thoroughly debauched. The purple flush on his face had spread to his ears and shoulders, and his chest rose and fell rapidly as he stared at Caleb with hungry, half-lidded eyes. The way Essek was sprawled across the bed, so elegant and delicate looking in his expensive lingerie on the fancy silk sheets, made a pang of arousal travel through Caleb's abdomen.

With Essek lying back on the bed with his legs spread so very invitingly for Caleb, Caleb could even see the wet spot soaking through to the outside of Essek's lacey underwear. Caleb withheld an embarrassing whimper at the sight of it.

"I need to fuck you before you take this off." Caleb blurted out, voice much rougher than intended. Essek didn't seem to mind though, judging by the little shiver that went down his spine when he heard Caleb's voice.

"What's stopping you?"

Caleb was positive he had never undressed and put his harness on so fast in his entire life.

When Caleb was done, he tossed a bottle of oil towards Essek, who was still lying on the bed where Caleb had placed him. "Prepare yourself for me. I want to watch you."

Essek seemed to flush even harder at that, but he wasted no time following Caleb's request, quickly sitting up and grabbing the bottle of oil. Essek reached down with his other hand and started to remove the underwear, but Caleb wasn't ready to let Essek take them off yet. He still wanted more time to memorize the way Essek looked wrapped in expensive lace and silk. Without even thinking about it, he was already reaching out to interrupt Essek's current course of action.

"Leave them on."

Essek let out a little laugh. "And how do you suppose I'm going to prepare myself with these on?"

Caleb didn't answer, instead reaching down and using one of his hands to simply pull the thin, delicate material to the side, leaving Essek's soaked cunt and throbbing clit in perfect view. Essek shivered, and his voice was weaker when he spoke again. "I see."

There were a few seconds where nothing happened. Caleb simply stared at Essek's soft, glistening folds, just barely resisting the urge to touch. He wanted to watch Essek do it himself, and he was ready to wait for it.

"Are- are you just going to stand there and watch?" Essek asked, suddenly a bit shyer than he was a few minutes ago. Caleb usually did this for him. In fact, Caleb wasn't sure if Essek had ever had the chance to prepare himself in front of Caleb with how excited Caleb usually was to get his hands on, and  _ inside  _ of Essek. There was no time like the present to have Essek try something new, though.

"I think I will,  _ ja _ ." Caleb grinned.

"Um- I- alright then." Essek muttered, shaking hands moving to uncork the vial of oil.

Caleb attentively watched every single movement as Essek drizzled the oil over his fingers before bringing them down between his thighs, almost gingerly parting those slick, soft folds to expose the entrance to his cunt. Essek's breath hitched a little as he slid in one finger, and then another right after the first. Essek glanced up towards Caleb every now and then, like he was making sure Caleb still approved of what was happening, which Caleb adored.

"I prefer yours." Essek gasped, somewhat sheepishly, as he began to fuck himself with his own fingers.

Caleb knew why. Essek's fingers weren't as large as his, and Essek craved the feeling of being full in the way only Caleb could make him feel. Caleb occasionally even caught Essek staring at his hands in public for longer than was strictly normal, and Caleb could tell exactly what was on Essek's mind every time.

Essek was eventually working a third finger inside of himself, quiet little moans spilling out of him as he thrust his slender fingers in and out of himself. Wet, slick noises from Essek's cunt were audible above Essek's soft sounds. Caleb could see Essek's clit throbbing, and he pulled the lace underwear even further out of Essek's way. Caleb was holding it out of the way instead of making Essek do it himself so that Essek could have both hands free to pleasure himself, but only one of Essek's hands was currently occupied. Caleb sought to remedy that.

"Use your other hand as well. I want to watch you make yourself come."

Essek moaned properly at Caleb's request, but nodded and quickly brought his other hand down between his thighs. Essek was rubbing at his clit with one hand now, and the other had three fingers buried knuckle deep inside of himself, Essek's shaking hands barely able to keep a consistent pace. Now that Essek was paying more attention to his neglected clit he quickly found himself getting closer, his hips rocking into the movements with every little thrust of his fingers.

While Caleb watched Essek, he oiled up the cock that he had attached to the harness- which was quite the feat with just one hand- but he managed with only a few spilled drops.

Essek looked up right as Caleb had the cock fisted in his hand, slowly stroking it up and down to spread the oil across the surface, and just like that, Essek was coming with an absolutely ruined noise. The sight of Caleb above him, lazily stroking his cock with one hand as he watched Essek finger himself was simply too much for Essek. He clenched tightly around his fingers as he came, though it wasn't nearly as tight as he would have been around Caleb's larger fingers. Essek found himself missing Caleb's fingers once more, vaguely realizing that his orgasms just weren't as satisfying when Caleb wasn't at least partially responsible for making him come.

"I want you in me." Essek gasped, not even having fully rode out his last orgasm yet before he was asking Caleb to fuck him. Caleb grinned at Essek's enthusiasm.

"Eager, are we?" Caleb teased softly, as he gestured for Essek to scoot further up the bed. When Essek obliged, Caleb crawled onto the bed and settled on his knees between Essek's legs.

"Only for you."

Caleb's heart fluttered a little at that, but he didn't falter in his movements. He hooked his hands around the back of Essek's knees and started to slowly push them up- bending Essek's legs in half and back towards Essek's shoulders. Caleb raised an eyebrow at Essek as he positioned him, making sure the position wasn't starting to get uncomfortable for Essek, not quite sure what the limits of the other's flexibility were. Luckily, Essek seemed plenty lithe enough, and he gave Caleb a quick small nod, not resisting even when Caleb had put almost his full body weight into bending Essek in half.

"Move those for me?" Caleb nodded towards the lacey material that was just barely covering Essek's cunt, and Essek shivered before nodding again. Essek pulled them to the side with a shaking hand, giving Caleb full access to his dripping cunt once more.

Caleb had to work a little harder to get the head of the cock inside of Essek, as both of his hands were currently occupied holding Essek's legs in place, which Essek took notice of, luckily. Essek used his free hand to help, guiding Caleb's cock into him eagerly.

Once the head was in, Caleb buried the rest inside of Essek in one swift thrust, making Essek cry out and throw his head back against the pillow. The encouraging noises spurred Caleb on further, and he pulled back until his cock was halfway out before snapping his hips back home. Essek's volume climbed even higher, and Caleb delighted in the fact that he was the only one who could make Essek sound the way he did currently.

Caleb's pace was fervent and relentless, a week or so of pent up frustration now making its way to the surface and spilling over. His thrusts were harsh and forceful, so much so that one of Essek's hands flew up to brace against the headboard to prevent himself from sliding further up the mattress, but Caleb knew Essek loved every second. The endless stream of moans and whimpers spilling from Essek's mouth were proof that Essek was loving the rough treatment that Caleb so enthusiastically provided for him.

The toy provided a pleasurable grinding pressure against Caleb's cock, and he found himself quickly getting wrapped up in all of the sensations around him, bringing him closer to the edge rapidly. It was hard not to feel a little overwhelmed by everything- the way Essek sounded, the way Essek  _ looked _ \- It was only a matter of time before Caleb's had to release his hold on Essek's thighs, a choked moan leaving him as he leaned over Essek and buried his face into Essek's neck. Blood was rushing in his ears as he came hard, his quick little puffs of breath ghosting across the sensitive flesh of Essek's delicate collarbones.

Caleb slowly rocked into Essek as he rode out his orgasm, and Essek took the opportunity to shove a hand between where their bodies were pressed together. Caleb hummed approvingly and mouthed kisses against Essek's neck and jawline, encouraging Essek to continue.

Essek rubbed his clit in small little circles, and his thighs were quickly trembling with the building force of his climax, not needing much to get him close with Caleb's cock still buried deep inside him. Just as Caleb could tell Essek was right on the edge, he thrust his hips into Essek hard and without warning. As Caleb expected, he only needed to deliver a few rough thrusts before Essek was keening and coming around the cock, his back arching off the sheets as he came.

Essek collapsed back to the sheets after the peak of his orgasm came and went, clearly exhausted after such intense activity, and Caleb felt much the same.

They stayed together like that for some time, with Essek beneath Caleb, looking gorgeously disheveled and fucked out as he caught his breath. Essek's breathing slowly returned to normal until the room was peaceful once more. The silence was both comfortable and welcome as they took the quiet passing of time as a chance to recuperate.

Essek eventually became the first one to interrupt the silence, or perhaps maybe they were both responsible. Essek tugged gently at the hair on the back of Caleb's neck, and when Caleb pulled his head away from where it was buried in Essek's neck, Essek's lips were suddenly on his. Caleb couldn't dream of resisting. It was a surprisingly sweet kiss, gentler than Caleb was expecting. He matched Essek's pace easily, and an undetermined amount of time was spent in soft kisses and tender touches.

When they finally broke apart, it was so Caleb could slide the cock out of Essek, resulting in a soft whimper of a complaint. Caleb gave Essek a few more gentle kisses as an apology before he was standing in order to unbuckle the harness and slide it off of himself.

Caleb methodically cleaned and put everything away, even helping Essek to remove the bralette when Essek started to fumble with it behind his back. Caleb withheld all of his teasing comments about Essek not being able to take a bra off. It made sense, really. Essek didn't commonly wear them (or at least Caleb was pretty sure he didn't, though he had half a mind to ask Essek to start now), and it wasn't like Essek was regularly removing the undergarments of anyone else besides Caleb. 

As they settled into bed in a blissfully familiar tangle of limbs, a thought occurred to Caleb.

"Essek, what are your measurements?" 

Essek let out a huff of laughter at the unexpected question. "I don't know off the top of my head. Why do you ask?"

"I'll need them in order to commission more lingerie for you."


End file.
